Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
  • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
  • A61K8/418—Amines containing nitro groups

Definitions

• the subject of the present invention is the use of monobenzene nitroanilines comprising at least one cationic group chosen from chains aliphatics comprising at least one cationic charge delocalized on a unsaturated polyazotated heterocycle with 5 links, their use as a dye direct in dyeing applications for keratin materials, in particular human keratin fibers, and in particular the hair, and more particularly the dye compositions containing them.
• nitroanilines have certainly already been described but their cationic charge is localized on the nitrogen atom of a aliphatic chain.
• Such nitroanilines are for example described in the U.S. Patent Nos. 5,135,543 and 5,256,823.
• cationic monobenzene nitroanilines of which at least one cationic charge is delocalized on a polyazotated heterocycle with 5 chains and therefore comprising at least one cationic group Z, Z being chosen from quaternized aliphatic chains, aliphatic chains comprising at least one saturated quaternized ring and aliphatic chains comprising at least one quaternized unsaturated cycle, suitable for use as direct dyes for dyeing direct, but in addition that they make it possible to obtain dye compositions leading to powerful and varied colorings having excellent properties of resistance to the various aggressions which the hair can undergo (light, friction, bad weather, friction, shampoos, perspiration) and significantly improved, compared to those of the dyes produced with cationic nitroanilines known from the prior art, the cationic charge of which is localized on the nitrogen atom of an aliphatic chain.
• these nitroanilines exhibit better solubility in
• alkyl and alkoxy radicals mentioned above in formulas (I), (II), (III) and (IV) can be linear or branched.
• the cationic monobenzene nitroanilines of formula (I) can be optionally salified with strong mineral acids such as HCI, HBr, H 2 SO 4 , or organic acids such as acetic, lactic, tartaric, citric or succinic.
• cycles of the unsaturated groups Z of formula (III) above it is possible to in particular, by way of example, mention the pyridine, pyrimidine cycles, pyrazine, oxazine and triazine.
• the quaternization stage is, generally for convenience, the last stage of synthesis, but can intervene earlier in the sequence of reactions leading to the preparation of the compounds of formula (I).
• a subject of the invention is also a composition for dyeing materials keratinous, characterized in that it comprises, in an appropriate medium for dyeing, an effective amount of at least one cationic nitroaniline monobenzene of formula (I) described above.
• the invention also relates to a composition for the direct dyeing of human keratin fibers, such as the hair, characterized by the fact that it comprises, in a medium suitable for dyeing, an effective amount at least one cationic monobenzene nitroaniline as defined above by formula (I).
• Another subject of the invention is the use of cationic nitroanilines monobenzenics of formula (I), as direct dyes, in, or for the preparation of, dye compositions for keratin materials.
• the cationic monobenzene nitroaniline (s) of formula (I) in accordance with the invention and / or the addition salt (s) with an acid preferably represent from 0.005 to 12% by weight approximately of the total weight of the dye composition, and even more preferably from 0.05 to 6% by weight about this weight.
• the cationic monobenzene nitroanilines of formula (I) can also serve, in well-known oxidation dyeing processes, using oxidation dyes (oxidation dye precursors and possibly couplers), to shade or enrich with reflections the dyes obtained with oxidation dyes.
• oxidation dyes oxidation dye precursors and possibly couplers
• the dye composition according to the invention may also contain, in order to widen the palette of shades and obtain varied shades, in addition to the cationic monobenzene nitroanilines of formula (I), other direct dye (s) conventionally used.
• benzene nitro dyes other than the cationic monobenzene nitroanilines of formula (I) according to the present invention and such as nitrophenylenediamines, nitrodiphenylamines, nitrated phenol ethers or nitrophenols, nitropyridines, anthraquinone dyes, dyes mono- or diazo, triarylmethanic, azinic, acridinic and xantheneic, or metalliferous dyes.
• the proportion of all these other direct addition dyes can vary between approximately 0.05 and 10% by weight relative to the total weight of the dye composition.
• the medium suitable for dyeing generally consists of water or a mixture of water and at least one organic solvent to dissolve the compounds which are not sufficiently soluble in water.
• organic solvent mention may, for example, be made of lower C 1 -C 4 alkanols, such as ethanol and isopropanol; glycerol; glycols and glycol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, similar products and mixtures thereof.
• the solvents may be present in proportions preferably of between 1 and 40% by weight relative to the total weight of the dye composition, and more preferably still between 5 and 30% by weight approximately. It is also possible to add to the composition according to the invention fatty amides such as mono- and di-ethanolamides of acids derived from coconut, lauric acid or oleic acid, at concentrations of between approximately 0.05 and 10% by weight.
• compositions according to the invention surfactants well known from the prior art and of anionic, cationic, nonionic, amphoteric, zwitterionic type or their mixtures, preferably in a proportion of between about 0.1 and 50% by weight and advantageously between about 1 and 20% by weight relative to the total weight of the composition.
• Thickening agents can also be used in an amount ranging from about 0.2 to 5%.
• Said dye composition may also contain various usual adjuvants such as antioxidants, perfumes, sequestering agents, dispersing agents, hair conditioning agents, preserving agents, opacifying agents, as well as any other adjuvant used usually in tincture of keratin materials.
• those skilled in the art will take care to choose the optional compound (s) mentioned above, in such a way that the advantageous properties intrinsically attached to the dye composition according to the invention are not, or not substantially, altered. by the addition (s) envisaged.
• the dye composition according to the invention can be formulated at acidic, neutral pH or alkaline, the pH possibly varying between 3 and 12 approximately and preferably between 5 and 11 approximately. It can be adjusted to the desired value using acidifying agents or basifying agents or buffers usually used in dyeing materials keratinous.
• the acidifying agents are conventionally mineral or organic acids such as, for example, hydrochloric, orthophosphoric, sulfuric acids, carboxylic acids such as acetic, tartaric, citric, lactic and sulfonic acids.
• buffers mention may be made, for example, of potassium diacid phosphate / sodium hydroxide.
• basifying agents there may be mentioned, by way of example, ammonia, alkali carbonates, alkanolamines such as mono- di- and tri-ethanolamines and their derivatives, sodium or potassium hydroxides, and compounds of formula: in which, W is a propylene residue optionally substituted by a hydroxyl group or a C 1 -C 4 alkyl radical; R 11 R 12, R 13 and R 14, simultaneously or independently of one another, represent a hydrogen atom, an alkyl radical C 1 -C 6 alkyl or hydroxy C 1 -C 6.
• composition applied to the hair can be in forms various, such as liquid, cream, gel or any other suitable form for dyeing keratin materials.
• it can be packaged under pressure in an aerosol can in presence of a propellant and form a foam.
• Another object of the present invention relates to a process for dyeing keratin fibers, in particular human keratin fibers such as the hair, by direct dyeing, consisting in allowing a dye composition containing at least one cationic monobenzene nitroaniline of formula (I) to act. ) on dry or wet keratin fibers.
• the composition according to the invention can be used as a leave-in composition, that is to say that after application of the composition to the fibers, it is dried without intermediate rinsing.
• the composition is left to act on the fibers for an exposure time varying between 3 and 60 minutes approximately, preferably between 5 and 45 minutes approximately, rinsed, optionally washed, then rinsed again , and we dry.
• Example 5 The procedure used was described for Example 5 (Step 4). From 49.0 g (0.2 mole) of (2-bromo-ethyl) - (4-nitro-phenyl) -amine (RN 55851-35-9) and from 19.8 g (0.24 mole) of 1 -methyl-1H-imidazole (RN 616-47-7) in 200ml of toluene, pale yellow crystals (62.3g) of 3-methyl-1- [2- (4-nitro-phenylamino) bromide were obtained -ethyl] -3H-imidazol-1-ium melting at 214 ° C (Kofler) and whose elemental analysis calculated for C 12 H 15 N 4 O 2 Br was: % VS H NOT O Br Calculated 44.05 4.62 17.12 9.78 24.42 Find 44.14 4.57 17.03 9.78 24.37
• the following dye composition was prepared: (all contents expressed in grams - MA stands for Active Material) Dye of formula (I) ll 0.484 Hydroxyethylcellulose sold under the name NATROSOL 250 MR by the company Aqualon 0.72 Benzyl alcohol 4 Polyethylene glycol with 6 ethylene oxide 6 Alkyl (C8-C10) polyglucoside in aqueous solution at 60% MA sold under the name ORAMIX CG 110 by the company Seppic 4.5 MA Phosphate buffer pH 7 qs 100
• the above composition was applied to locks of natural gray hair or permed to 90% white and left to stand for 20 minutes. After rinsing with running water and drying, the hair was dyed in a shade intense yellow.
• composition of Example 2 yellow Composition of Example 3 yellow Composition of Example 4 yellow Composition of Example 5 yellow Composition of Example 6 copper gold Composition of Example 7 copper gold

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• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Birds (AREA)
• Epidemiology (AREA)
• Cosmetics (AREA)

Applications Claiming Priority (2)

Publications (3)

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Family Applications (1)

Country Status (14)

Cited By (1)

Families Citing this family (4)

Family Cites Families (22)

• 1999
  • 1999-01-08 FR FR9900151A patent/FR2788221B1/fr not_active Expired - Fee Related
  • 1999-12-16 DE DE69930095T patent/DE69930095T2/de not_active Expired - Fee Related
  • 1999-12-16 EP EP99403170A patent/EP1018333B1/de not_active Expired - Lifetime
  • 1999-12-16 AT AT99403170T patent/ATE318641T1/de not_active IP Right Cessation
• 2000
  • 2000-01-06 BR BR0000562-2A patent/BR0000562A/pt not_active IP Right Cessation
  • 2000-01-06 RU RU2000100462/14A patent/RU2203646C2/ru not_active IP Right Cessation
  • 2000-01-06 CA CA002294892A patent/CA2294892A1/fr not_active Abandoned
  • 2000-01-07 US US09/479,239 patent/US6478827B1/en not_active Expired - Fee Related
  • 2000-01-07 AR ARP000100051A patent/AR018213A1/es not_active Application Discontinuation
  • 2000-01-07 CN CNB001025287A patent/CN1191051C/zh not_active Expired - Fee Related
  • 2000-01-07 PL PL00337748A patent/PL337748A1/xx not_active Application Discontinuation
  • 2000-01-07 KR KR1020000000693A patent/KR100359147B1/ko not_active Expired - Fee Related
  • 2000-01-07 HU HU0000039A patent/HUP0000039A3/hu unknown
  • 2000-01-11 JP JP3069A patent/JP2000204028A/ja active Pending

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